Bromoacetic Acid → 4-Morpholineacetic acid

HRID 550333Notes

Reaction equation

HRID 550333 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>O1CCCC1>[N:6]1([CH2:2][C:3]([OH:5])=[O:4])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6227Bromoacetic AcidHCID 8083Morpholine

Product 1

HCID 4389684-Morpholineacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Bromoacetic acid (2 g, 14.4 mole) was dissolved in tetrahydrofuran (50 mL) and added dropwise to a stirred solution of morpholine (3.76 g, 43.2 mole) in tetrahydrofuran (THF, 20 mL). The solution was stirred at room temperature for three days. The white solid (4.17 g) was filtered, washed with THF (100 mL), and recrystallised from hot ethanol (EtOH), Yield: 2.59 g: IR:1740 cm−1. For the two different isobaric versions of morpholine acetic acid, either bromoacetic-1-13C acid (Aldrich PN 27,933-1) or bromoacetic-2-13C acid (Aldrich PN 27,935-8) was substituted for bromoacetic acid.

Workup

  1. filtrationThe white solid (4.17 g) was filtered
  2. washwashed with THF (100 mL)
  3. customrecrystallised from hot ethanol (EtOH), Yield: 2.59 g

Sources & evidence

ORD record
ord-9721f5ae3e5640198062d4adca78ff71
Source dataset
uspto-grants-2011_05
Patent number
US07947513B2

Reaction notes

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